diff --git a/nix/npm-deps.hash b/nix/npm-deps.hash
index d23e9ece2..a268f41ed 100644
--- a/nix/npm-deps.hash
+++ b/nix/npm-deps.hash
@@ -1 +1 @@
-sha256-Mg6cn08RoEFmAYKDjowYd7DZSeeJezix0rzQeDadRAs=
+sha256-WOVtBB7AQke7RM9FDJ1mUDU0sLMf03QOrvajrXSFwPs=
diff --git a/package-lock.json b/package-lock.json
index ad0390d58..a322f4b7f 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -7728,6 +7728,12 @@
       "integrity": "sha512-l0h88YhZFyKdXIFNfSWpyjStDjGHwZ/U7iobcK1cQQD8sejsONdQtTVU+1wVN1PBw40PiiHB1vA5S7VTfQiP9g==",
       "license": "MIT"
     },
+    "node_modules/@mixmark-io/domino": {
+      "version": "2.2.0",
+      "resolved": "https://registry.npmjs.org/@mixmark-io/domino/-/domino-2.2.0.tgz",
+      "integrity": "sha512-Y28PR25bHXUg88kCV7nivXrP2Nj2RueZ3/l/jdx6J9f8J4nsEGcgX0Qe6lt7Pa+J79+kPiJU3LguR6O/6zrLOw==",
+      "license": "BSD-2-Clause"
+    },
     "node_modules/@modelcontextprotocol/sdk": {
       "version": "1.29.0",
       "resolved": "https://registry.npmjs.org/@modelcontextprotocol/sdk/-/sdk-1.29.0.tgz",
@@ -12952,6 +12958,13 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/turndown": {
+      "version": "5.0.6",
+      "resolved": "https://registry.npmjs.org/@types/turndown/-/turndown-5.0.6.tgz",
+      "integrity": "sha512-ru00MoyeeouE5BX4gRL+6m/BsDfbRayOskWqUvh7CLGW+UXxHQItqALa38kKnOiZPqJrtzJUgAC2+F0rL1S4Pg==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/@types/unist": {
       "version": "3.0.3",
       "resolved": "https://registry.npmjs.org/@types/unist/-/unist-3.0.3.tgz",
@@ -33434,6 +33447,12 @@
         "domino": "^2.1.6"
       }
     },
+    "node_modules/turndown-plugin-gfm": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/turndown-plugin-gfm/-/turndown-plugin-gfm-1.0.2.tgz",
+      "integrity": "sha512-vwz9tfvF7XN/jE0dGoBei3FXWuvll78ohzCZQuOb+ZjWrs3a0XhQVomJEb2Qh4VHTPNRO4GPZh0V7VRbiWwkRg==",
+      "license": "MIT"
+    },
     "node_modules/tweetnacl": {
       "version": "1.0.3",
       "resolved": "https://registry.npmjs.org/tweetnacl/-/tweetnacl-1.0.3.tgz",
@@ -35388,6 +35407,8 @@
         "react-native-webview": "^13.16.0",
         "react-native-worklets": "~0.8.3",
         "tiny-invariant": "^1.3.3",
+        "turndown": "^7.2.4",
+        "turndown-plugin-gfm": "^1.0.2",
         "use-sync-external-store": "^1.6.0",
         "zod": "^4.4.3",
         "zustand": "^5.0.9"
@@ -35399,6 +35420,7 @@
         "@types/markdown-it": "^14.1.2",
         "@types/qrcode": "^1.5.6",
         "@types/react": "~19.2.0",
+        "@types/turndown": "^5.0.6",
         "@types/ws": "^8.18.1",
         "@vitest/browser": "^4.1.7",
         "@vitest/browser-playwright": "^4.1.7",
@@ -36237,6 +36259,19 @@
       "dev": true,
       "license": "MIT"
     },
+    "packages/app/node_modules/turndown": {
+      "version": "7.2.4",
+      "resolved": "https://registry.npmjs.org/turndown/-/turndown-7.2.4.tgz",
+      "integrity": "sha512-I8yFsfRzmzK0WV1pNNOA4A7y4RDfFxPRxb3t+e3ui14qSGOxGtiSP6GjeX+Y6CHb7HYaFj7ECUD7VE5kQMZWGQ==",
+      "license": "MIT",
+      "dependencies": {
+        "@mixmark-io/domino": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=18",
+        "npm": ">=9"
+      }
+    },
     "packages/app/node_modules/undici": {
       "version": "7.28.0",
       "resolved": "https://registry.npmjs.org/undici/-/undici-7.28.0.tgz",
diff --git a/packages/app/e2e/browser/assistant-selection-copy.spec.ts b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
new file mode 100644
index 000000000..2df4420ec
--- /dev/null
+++ b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
@@ -0,0 +1,315 @@
+import type { BrowserContext } from "@playwright/test";
+import { expect, test, type Page } from "../support/fixtures";
+import { openAgentRoute, seedMockAgentWorkspace } from "../support/helpers/mock-agent";
+
+const ASSISTANT_MARKDOWN = [
+  "Direct matches:",
+  "",
+  "Formatted **strong prose**, _emphasized prose_, and ~~struck prose~~.",
+  "",
+  "- **[First issue](https://example.com/issues/1)**: exact `apply_patch` failure.",
+  "- [Second issue](https://example.com/issues/2): repeated sandbox setup.",
+  "",
+  "5. Fifth item",
+  "6. Sixth item",
+  "7. Seventh item",
+  "8. Eighth item",
+  "",
+  "Nested list:",
+  "",
+  "3. Outer three",
+  "",
+  "   7. Inner seven",
+  "   8. Inner eight",
+  "   9. Inner nine",
+  "",
+  "A hard break  ",
+  "stays hard.",
+  "",
+  "www.example.com stays plain Markdown text.",
+  "",
+  '[docs](https://docs.example.com "Reference") and <https://autolink.example.com>.',
+  "",
+  "[workspace file](file:///tmp/paseo%20notes.md#L4)",
+  "",
+  "`https://example.com/generated` stays code, not a generated link.",
+  "",
+  "```typescript",
+  'const answer = "yes";',
+  "```",
+  "",
+  "````text",
+  "before",
+  "```",
+  "after",
+  "````",
+  "",
+  "| Left | Right | Center |",
+  "| :-- | --: | :-: |",
+  "| Current \\| active | ~~obsolete~~ | ready |",
+].join("\n");
+
+const EXPECTED_WHOLE_SELECTION_MARKDOWN = ASSISTANT_MARKDOWN.replace(
+  "<https://autolink.example.com>",
+  "[https://autolink.example.com](https://autolink.example.com)",
+).replace(
+  "3. Outer three\n\n   7. Inner seven\n   8. Inner eight\n   9. Inner nine",
+  "3. Outer three\n    7. Inner seven\n    8. Inner eight\n    9. Inner nine",
+);
+
+interface ClipboardContent {
+  html: string;
+  plainText: string;
+}
+
+async function allowRichClipboard(context: BrowserContext): Promise<void> {
+  await context.grantPermissions(["clipboard-read", "clipboard-write"]);
+}
+
+async function selectAssistantMessage(page: Page): Promise<void> {
+  const assistantMessage = page.getByTestId("assistant-message").filter({
+    hasText: "Direct matches:",
+  });
+  await expect(assistantMessage).toBeVisible();
+  await assistantMessage.evaluate((element) => {
+    const selection = window.getSelection();
+    const range = document.createRange();
+    range.selectNodeContents(element);
+    selection?.removeAllRanges();
+    selection?.addRange(range);
+  });
+}
+
+async function selectAssistantText(page: Page, text: string): Promise<void> {
+  await selectAssistantTextRange(page, text, text);
+}
+
+async function selectAssistantTextRange(
+  page: Page,
+  startText: string,
+  endText: string,
+): Promise<void> {
+  const assistantMessage = page.getByTestId("assistant-message").filter({
+    hasText: "Direct matches:",
+  });
+  await assistantMessage.evaluate(
+    (element, selectedRange) => {
+      const walker = document.createTreeWalker(element, NodeFilter.SHOW_TEXT);
+      let startNode: Node | null = null;
+      let startOffset = -1;
+      let endNode: Node | null = null;
+      let endOffset = -1;
+      let textNode = walker.nextNode();
+      while (textNode) {
+        if (!startNode) {
+          const offset = textNode.textContent?.indexOf(selectedRange.startText) ?? -1;
+          if (offset >= 0) {
+            startNode = textNode;
+            startOffset = offset;
+          }
+        }
+        if (startNode) {
+          const offset = textNode.textContent?.indexOf(selectedRange.endText) ?? -1;
+          if (offset >= 0) {
+            endNode = textNode;
+            endOffset = offset + selectedRange.endText.length;
+            break;
+          }
+        }
+        textNode = walker.nextNode();
+      }
+      if (!startNode || !endNode) {
+        throw new Error(
+          `Could not find assistant text range: ${selectedRange.startText} — ${selectedRange.endText}`,
+        );
+      }
+      const range = document.createRange();
+      range.setStart(startNode, startOffset);
+      range.setEnd(endNode, endOffset);
+      const selection = window.getSelection();
+      selection?.removeAllRanges();
+      selection?.addRange(range);
+    },
+    { startText, endText },
+  );
+}
+
+async function copySelection(page: Page): Promise<void> {
+  await page.keyboard.press("ControlOrMeta+c");
+}
+
+async function readRichClipboard(page: Page): Promise<ClipboardContent> {
+  return page.evaluate(async () => {
+    const items = await navigator.clipboard.read();
+    const item = items[0];
+    if (!item) {
+      throw new Error("Expected clipboard content");
+    }
+    return {
+      html: await (await item.getType("text/html")).text(),
+      plainText: await (await item.getType("text/plain")).text(),
+    };
+  });
+}
+
+test("copying an assistant selection preserves Markdown structure and links", async ({
+  context,
+  page,
+}) => {
+  await page.addInitScript(() => {
+    localStorage.setItem("@paseo:app-settings", JSON.stringify({ uiFontFamily: "serif" }));
+  });
+  const agent = await seedMockAgentWorkspace({
+    repoPrefix: "assistant-selection-copy-",
+    title: "Assistant selection copy",
+    initialPrompt: "Render the clipboard fixture.",
+    featureValues: { mockAssistantResponse: ASSISTANT_MARKDOWN },
+  });
+
+  try {
+    await allowRichClipboard(context);
+    await agent.client.waitForAgentUpsert(
+      agent.agentId,
+      (snapshot) => snapshot.status === "idle",
+      30_000,
+    );
+    await openAgentRoute(page, agent);
+
+    const assistantMessage = page.getByTestId("assistant-message").filter({
+      hasText: "Direct matches:",
+    });
+    for (const [tag, text] of [
+      ["strong", "strong prose"],
+      ["em", "emphasized prose"],
+      ["s", "struck prose"],
+    ]) {
+      const formattedProse = assistantMessage
+        .locator(`[data-paseo-markdown-tag="${tag}"]`)
+        .filter({ hasText: text });
+      await expect(formattedProse).toHaveCSS("font-family", "serif");
+      await expect(formattedProse).not.toHaveAttribute("data-pmono");
+    }
+    const inlineCode = assistantMessage
+      .locator('[data-paseo-markdown-tag="code"]')
+      .filter({ hasText: "apply_patch" });
+    await expect(inlineCode).toHaveAttribute("data-pmono", "");
+
+    await selectAssistantMessage(page);
+    await copySelection(page);
+
+    const clipboard = await readRichClipboard(page);
+    expect(clipboard.plainText).toBe(EXPECTED_WHOLE_SELECTION_MARKDOWN);
+    expect(clipboard.html).toContain("<ul>");
+    expect(clipboard.html).toContain(
+      '<strong><a href="https://example.com/issues/1">First issue</a></strong>',
+    );
+    expect(clipboard.html).toContain("<code>apply_patch</code>");
+    expect(clipboard.html).toContain('<ol start="5">');
+    expect(clipboard.html).toContain("A hard break<br>");
+    expect(clipboard.html).toContain(
+      '<a href="http://www.example.com/">www.example.com</a> stays plain Markdown text.',
+    );
+    expect(clipboard.html).toContain(
+      '<a href="https://docs.example.com/" title="Reference">docs</a>',
+    );
+    expect(clipboard.html).toContain(
+      '<a href="https://autolink.example.com/">https://autolink.example.com</a>',
+    );
+    expect(clipboard.html).toContain(
+      '<a href="file:///tmp/paseo%20notes.md#L4">workspace file</a>',
+    );
+    expect(clipboard.html).toContain("<code>https://example.com/generated</code>");
+    expect(clipboard.html).not.toContain(
+      '<a href="https://example.com/generated"><code>https://example.com/generated</code></a>',
+    );
+    expect(clipboard.html).toContain('<code class="language-typescript">');
+    expect(clipboard.html).toContain(
+      '<pre><code class="language-text">before\n```\nafter\n</code></pre>',
+    );
+    expect(clipboard.html).toContain("<table>");
+    expect(clipboard.html).toContain('<td style="text-align:left">Current | active</td>');
+    expect(clipboard.html.match(/<td\b/g)).toHaveLength(3);
+    expect(clipboard.html).toContain("<s>obsolete</s>");
+    expect(clipboard.html).toContain('<th style="text-align:left">Left</th>');
+    expect(clipboard.html).toContain('<th style="text-align:right">Right</th>');
+    expect(clipboard.html).toContain('<th style="text-align:center">Center</th>');
+
+    await selectAssistantText(page, "First");
+    await copySelection(page);
+
+    const partialClipboard = await readRichClipboard(page);
+    expect(partialClipboard.plainText).toBe("- **[First](https://example.com/issues/1)**");
+    expect(partialClipboard.html).toContain(
+      '<li><strong><a href="https://example.com/issues/1">First</a></strong></li>',
+    );
+
+    await selectAssistantText(page, "docs");
+    await copySelection(page);
+
+    const titledLinkClipboard = await readRichClipboard(page);
+    expect(titledLinkClipboard.plainText).toBe('[docs](https://docs.example.com "Reference")');
+    expect(titledLinkClipboard.html).toContain(
+      '<a href="https://docs.example.com/" title="Reference">docs</a>',
+    );
+
+    await selectAssistantText(page, "https://autolink.example.com");
+    await copySelection(page);
+
+    const autolinkClipboard = await readRichClipboard(page);
+    expect(autolinkClipboard.plainText).toBe(
+      "[https://autolink.example.com](https://autolink.example.com)",
+    );
+    expect(autolinkClipboard.html).toContain(
+      '<a href="https://autolink.example.com/">https://autolink.example.com</a>',
+    );
+
+    await selectAssistantText(page, "workspace file");
+    await copySelection(page);
+
+    const fileLinkClipboard = await readRichClipboard(page);
+    expect(fileLinkClipboard.plainText).toBe("[workspace file](file:///tmp/paseo%20notes.md#L4)");
+    expect(fileLinkClipboard.html).toContain(
+      '<a href="file:///tmp/paseo%20notes.md#L4">workspace file</a>',
+    );
+
+    await selectAssistantTextRange(page, "Seventh item", "Eighth item");
+    await copySelection(page);
+
+    const midListClipboard = await readRichClipboard(page);
+    expect(midListClipboard.plainText).toBe("7. Seventh item\n8. Eighth item");
+    expect(midListClipboard.html).toContain('<ol start="7">');
+
+    await selectAssistantTextRange(page, "Inner eight", "Inner nine");
+    await copySelection(page);
+
+    const nestedListClipboard = await readRichClipboard(page);
+    expect(nestedListClipboard.plainText).toBe("3. 8. Inner eight\n    9. Inner nine");
+    expect(nestedListClipboard.html).toContain('<ol start="8">');
+
+    await selectAssistantTextRange(page, "Seventh item", "Nested list:");
+    await copySelection(page);
+
+    const crossBlockClipboard = await readRichClipboard(page);
+    expect(crossBlockClipboard.plainText).toBe("7. Seventh item\n8. Eighth item\n\nNested list:");
+    expect(crossBlockClipboard.html).toContain('<ol start="7">');
+
+    await selectAssistantText(page, "Current");
+    await copySelection(page);
+
+    const partialTableClipboard = await readRichClipboard(page);
+    expect(partialTableClipboard.plainText).toBe("Current");
+    expect(partialTableClipboard.html).toContain("<p>Current</p>");
+    expect(partialTableClipboard.html).not.toContain("&lt;table");
+
+    await selectAssistantTextRange(page, "Right", "ready");
+    await copySelection(page);
+
+    const columnSliceClipboard = await readRichClipboard(page);
+    expect(columnSliceClipboard.plainText).toContain("ready");
+    expect(columnSliceClipboard.html).not.toContain("<table>");
+    expect(columnSliceClipboard.html).toContain("ready");
+    expect(columnSliceClipboard.html).toContain("<s>obsolete</s>");
+  } finally {
+    await agent.cleanup();
+  }
+});
diff --git a/packages/app/package.json b/packages/app/package.json
index 280a0217f..a7c88f74c 100644
--- a/packages/app/package.json
+++ b/packages/app/package.json
@@ -113,6 +113,8 @@
     "react-native-webview": "^13.16.0",
     "react-native-worklets": "~0.8.3",
     "tiny-invariant": "^1.3.3",
+    "turndown": "^7.2.4",
+    "turndown-plugin-gfm": "^1.0.2",
     "use-sync-external-store": "^1.6.0",
     "zod": "^4.4.3",
     "zustand": "^5.0.9"
@@ -124,6 +126,7 @@
     "@types/markdown-it": "^14.1.2",
     "@types/qrcode": "^1.5.6",
     "@types/react": "~19.2.0",
+    "@types/turndown": "^5.0.6",
     "@types/ws": "^8.18.1",
     "@vitest/browser": "^4.1.7",
     "@vitest/browser-playwright": "^4.1.7",
diff --git a/packages/app/src/agent-stream/view.tsx b/packages/app/src/agent-stream/view.tsx
index 980925dc2..a23c60657 100644
--- a/packages/app/src/agent-stream/view.tsx
+++ b/packages/app/src/agent-stream/view.tsx
@@ -84,6 +84,7 @@ import {
   type BottomAnchorRouteRequest,
 } from "./bottom-anchor-controller";
 import { createAssistantImageOccurrenceKey } from "@/assistant-image/acquisition-cache";
+import { AssistantSelectionCopySurface } from "@/assistant-selection-copy/surface";
 import {
   AssistantFileLinkResolverProvider,
   normalizeInlinePathTarget,
@@ -976,7 +977,7 @@ const AgentStreamViewComponent = forwardRef<AgentStreamViewHandle, AgentStreamVi
 
     return (
       <ToolCallSheetProvider>
-        <View style={stylesheet.container}>
+        <AssistantSelectionCopySurface style={stylesheet.container}>
           <MessageOuterSpacingProvider disableOuterSpacing>
             {streamRenderStrategy.render({
               agentId,
@@ -1021,7 +1022,7 @@ const AgentStreamViewComponent = forwardRef<AgentStreamViewHandle, AgentStreamVi
               </Animated.View>
             </View>
           )}
-        </View>
+        </AssistantSelectionCopySurface>
       </ToolCallSheetProvider>
     );
   },
diff --git a/packages/app/src/assistant-file-links/link.tsx b/packages/app/src/assistant-file-links/link.tsx
index d209411ac..d99188cff 100644
--- a/packages/app/src/assistant-file-links/link.tsx
+++ b/packages/app/src/assistant-file-links/link.tsx
@@ -16,6 +16,7 @@ import { Shortcut } from "@/components/ui/shortcut";
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
 import { useStableEvent } from "@/hooks/use-stable-event";
 import { CODE_SURFACE_DATASET } from "@/styles/code-surface";
+import { markdownCopyDataSet } from "@/assistant-selection-copy/markup";
 import { useAssistantFileLinkResolverContext } from "./provider";
 import type { AssistantFileLinkSource } from "./resolver";
 import { useFileLink } from "./use-file-link";
@@ -27,6 +28,11 @@ interface AssistantMarkdownLinkProps {
   children: ReactNode;
 }
 
+const MARKDOWN_CODE_LINK_DATASET = {
+  ...CODE_SURFACE_DATASET,
+  ...markdownCopyDataSet.code,
+} as const;
+
 export function AssistantMarkdownLink({
   source,
   style,
@@ -62,6 +68,7 @@ export function AssistantMarkdownLink({
     () => ({ onPress, accessibilityRole: "link" }),
     [onPress],
   );
+  const unwrapForMarkdownCopy = source.sourceType === "inline-code" || source.markup === "linkify";
 
   if (isNative) {
     // Must be a MarkdownTextSpan, not a plain <Text>: on iOS the link renders
@@ -100,7 +107,9 @@ export function AssistantMarkdownLink({
 
   const anchor = (
     <a
+      {...(unwrapForMarkdownCopy ? { "data-paseo-markdown-unwrap": "true" } : {})}
       href={source.href}
+      title={source.title}
       onClickCapture={handleAnchorClickCapture}
       onAuxClickCapture={preventAnchorNavigation}
       style={LINK_ANCHOR_STYLE}
@@ -111,7 +120,10 @@ export function AssistantMarkdownLink({
         onHoverIn={handleHoverIn}
         onHoverOut={handleHoverOut}
       >
-        <Text dataSet={monoSurface ? CODE_SURFACE_DATASET : undefined} style={hoveredTextStyle}>
+        <Text
+          dataSet={monoSurface ? MARKDOWN_CODE_LINK_DATASET : undefined}
+          style={hoveredTextStyle}
+        >
           {children}
         </Text>
       </Pressable>
diff --git a/packages/app/src/assistant-file-links/resolver.ts b/packages/app/src/assistant-file-links/resolver.ts
index 30102fdf8..5fa4849fc 100644
--- a/packages/app/src/assistant-file-links/resolver.ts
+++ b/packages/app/src/assistant-file-links/resolver.ts
@@ -9,6 +9,7 @@ import { i18n } from "@/i18n/i18next";
 export interface AssistantFileLinkSource {
   href: string;
   text?: string;
+  title?: string;
   markup?: string;
   sourceInfo?: string;
   sourceType?: "inline-code";
diff --git a/packages/app/src/assistant-file-links/use-file-link.ts b/packages/app/src/assistant-file-links/use-file-link.ts
index 80c17348d..0ce4515b0 100644
--- a/packages/app/src/assistant-file-links/use-file-link.ts
+++ b/packages/app/src/assistant-file-links/use-file-link.ts
@@ -242,10 +242,10 @@ function canResolveAssistantFileLinkToFile(
 }
 
 function useStableSource(source: AssistantFileLinkSource): AssistantFileLinkSource {
-  const { href, text, markup, sourceInfo, sourceType } = source;
+  const { href, text, title, markup, sourceInfo, sourceType } = source;
   return useMemo(
-    () => ({ href, text, markup, sourceInfo, sourceType }),
-    [href, text, markup, sourceInfo, sourceType],
+    () => ({ href, text, title, markup, sourceInfo, sourceType }),
+    [href, text, title, markup, sourceInfo, sourceType],
   );
 }
 
diff --git a/packages/app/src/assistant-selection-copy/content.web.ts b/packages/app/src/assistant-selection-copy/content.web.ts
new file mode 100644
index 000000000..9a49d2c2a
--- /dev/null
+++ b/packages/app/src/assistant-selection-copy/content.web.ts
@@ -0,0 +1,212 @@
+import TurndownService from "turndown";
+import { gfm } from "turndown-plugin-gfm";
+import {
+  createMarkdownClipboardContent,
+  type MarkdownClipboardContent,
+} from "@/utils/rich-clipboard";
+import {
+  MARKDOWN_COPY_ALIGN_ATTRIBUTE,
+  MARKDOWN_COPY_IGNORE_ATTRIBUTE,
+  MARKDOWN_COPY_LANGUAGE_ATTRIBUTE,
+  MARKDOWN_COPY_LIST_START_ATTRIBUTE,
+  MARKDOWN_COPY_TAG_ATTRIBUTE,
+  MARKDOWN_COPY_UNWRAP_ATTRIBUTE,
+} from "./markup";
+
+const ASSISTANT_MESSAGE_SELECTOR = '[data-testid="assistant-message"]';
+
+const turndown = new TurndownService({
+  bulletListMarker: "-",
+  codeBlockStyle: "fenced",
+  emDelimiter: "_",
+  strongDelimiter: "**",
+});
+turndown.use(gfm);
+turndown.addRule("escapedGfmTableCell", {
+  filter: ["th", "td"],
+  replacement: (content, node) => {
+    const index = node.parentNode ? Array.from(node.parentNode.childNodes).indexOf(node) : 0;
+    const prefix = index === 0 ? "| " : " ";
+    return `${prefix}${content.replace(/\|/g, "\\|")} |`;
+  },
+});
+turndown.addRule("gfmStrikethrough", {
+  filter: ["del", "s"],
+  replacement: (content) => `~~${content}~~`,
+});
+turndown.addRule("compactListItem", {
+  filter: "li",
+  replacement: (content, node, options) => {
+    const item = content
+      .replace(/^\n+/, "")
+      .replace(/\n+$/, "\n")
+      .replace(/\n(?=\S)/g, "\n    ");
+    const parent = node.parentElement;
+    if (parent?.nodeName !== "OL") {
+      return `${options.bulletListMarker} ${item}\n`;
+    }
+    const start = Number(parent.getAttribute("start") ?? 1);
+    const index = Array.from(parent.children).indexOf(node);
+    return `${start + index}. ${item}\n`;
+  },
+});
+
+export function createAssistantSelectionClipboardContent(
+  selection: Selection | null,
+): MarkdownClipboardContent | null {
+  if (!selection || selection.rangeCount !== 1 || selection.isCollapsed) {
+    return null;
+  }
+
+  const range = selection.getRangeAt(0);
+  const startMessage = closestAssistantMessage(range.startContainer);
+  const endMessage = closestAssistantMessage(range.endContainer);
+  if (!startMessage || startMessage !== endMessage) {
+    return null;
+  }
+
+  const container = document.createElement("div");
+  const selected = wrapSelectionWithAncestors(range, startMessage);
+  normalizeOrderedListStarts(selected, range, startMessage);
+  container.append(selected);
+  restoreMarkdownElements(container);
+
+  const markdown = turndown.turndown(container.innerHTML).trim();
+  return markdown ? createMarkdownClipboardContent(markdown) : null;
+}
+
+function wrapSelectionWithAncestors(range: Range, message: Element): Node {
+  let selected: Node = range.cloneContents();
+  let ancestor =
+    range.commonAncestorContainer instanceof Element
+      ? range.commonAncestorContainer
+      : range.commonAncestorContainer.parentElement;
+
+  while (ancestor && ancestor !== message) {
+    const wrapper = ancestor.cloneNode(false) as Element;
+    wrapper.append(selected);
+    selected = wrapper;
+    ancestor = ancestor.parentElement;
+  }
+
+  return selected;
+}
+
+function normalizeOrderedListStarts(selected: Node, range: Range, message: Element): void {
+  const selector = `[${MARKDOWN_COPY_TAG_ATTRIBUTE}="ol"]`;
+  const originals = Array.from(message.querySelectorAll(selector)).filter((list) =>
+    range.intersectsNode(list),
+  );
+  const copies = markedElements(selected, selector);
+
+  for (let index = 0; index < Math.min(originals.length, copies.length); index += 1) {
+    const original = originals[index];
+    const firstSelectedItem = Array.from(original.children).find(
+      (child) =>
+        child.getAttribute(MARKDOWN_COPY_TAG_ATTRIBUTE) === "li" && range.intersectsNode(child),
+    );
+    if (!firstSelectedItem) {
+      continue;
+    }
+    const omittedItems = Array.from(original.children)
+      .slice(0, Array.from(original.children).indexOf(firstSelectedItem))
+      .filter((child) => child.getAttribute(MARKDOWN_COPY_TAG_ATTRIBUTE) === "li").length;
+    const originalStart = Number(original.getAttribute(MARKDOWN_COPY_LIST_START_ATTRIBUTE) ?? 1);
+    copies[index].setAttribute(
+      MARKDOWN_COPY_LIST_START_ATTRIBUTE,
+      String(originalStart + omittedItems),
+    );
+  }
+}
+
+function markedElements(root: Node, selector: string): Element[] {
+  const elements = root instanceof Element && root.matches(selector) ? [root] : [];
+  if ("querySelectorAll" in root) {
+    elements.push(...Array.from((root as ParentNode).querySelectorAll(selector)));
+  }
+  return elements;
+}
+
+function closestAssistantMessage(node: Node): Element | null {
+  const element = node instanceof Element ? node : node.parentElement;
+  return element?.closest(ASSISTANT_MESSAGE_SELECTOR) ?? null;
+}
+
+function restoreMarkdownElements(container: HTMLElement): void {
+  for (const ignored of container.querySelectorAll(`[${MARKDOWN_COPY_IGNORE_ATTRIBUTE}]`)) {
+    ignored.remove();
+  }
+
+  const marked = Array.from(container.querySelectorAll(`[${MARKDOWN_COPY_TAG_ATTRIBUTE}]`));
+  for (const element of marked.toReversed()) {
+    const tagName = element.getAttribute(MARKDOWN_COPY_TAG_ATTRIBUTE);
+    if (!tagName) {
+      continue;
+    }
+    const semanticElement = document.createElement(tagName);
+    if (tagName !== "br") {
+      semanticElement.append(...element.childNodes);
+    }
+    if (tagName === "ol") {
+      const start = element.getAttribute(MARKDOWN_COPY_LIST_START_ATTRIBUTE);
+      if (start) {
+        semanticElement.setAttribute("start", start);
+      }
+    }
+    if (tagName === "pre") {
+      const language = element.getAttribute(MARKDOWN_COPY_LANGUAGE_ATTRIBUTE);
+      const code = semanticElement.querySelector(":scope > code");
+      if (language && code) {
+        code.className = `language-${language}`;
+      }
+    }
+    if (tagName === "th" || tagName === "td") {
+      const alignment = element.getAttribute(MARKDOWN_COPY_ALIGN_ATTRIBUTE);
+      if (alignment) {
+        semanticElement.setAttribute("align", alignment);
+      }
+    }
+    element.replaceWith(semanticElement);
+  }
+
+  unwrapIncompleteTables(container);
+
+  const generatedLinks = Array.from(
+    container.querySelectorAll(`[${MARKDOWN_COPY_UNWRAP_ATTRIBUTE}]`),
+  );
+  for (const element of generatedLinks.toReversed()) {
+    element.replaceWith(...element.childNodes);
+  }
+
+  const presentational = Array.from(container.querySelectorAll("div, span"));
+  for (const element of presentational.toReversed()) {
+    element.replaceWith(...element.childNodes);
+  }
+}
+
+function unwrapIncompleteTables(container: HTMLElement): void {
+  for (const table of container.querySelectorAll("table")) {
+    if (hasUsableTableColumnContract(table)) {
+      continue;
+    }
+    const cells = Array.from(table.querySelectorAll("th, td"));
+    const selectedContent = document.createDocumentFragment();
+    cells.forEach((cell, index) => {
+      if (index > 0) {
+        selectedContent.append("\n");
+      }
+      selectedContent.append(...cell.childNodes);
+    });
+    table.replaceWith(selectedContent);
+  }
+}
+
+function hasUsableTableColumnContract(table: Element): boolean {
+  const headerWidth = table.querySelectorAll("thead th").length;
+  return (
+    headerWidth > 0 &&
+    Array.from(table.querySelectorAll("tbody tr")).every(
+      (row) => row.children.length <= headerWidth,
+    )
+  );
+}
diff --git a/packages/app/src/assistant-selection-copy/markup.ts b/packages/app/src/assistant-selection-copy/markup.ts
new file mode 100644
index 000000000..9191b850a
--- /dev/null
+++ b/packages/app/src/assistant-selection-copy/markup.ts
@@ -0,0 +1,63 @@
+export const MARKDOWN_COPY_TAG_ATTRIBUTE = "data-paseo-markdown-tag";
+export const MARKDOWN_COPY_IGNORE_ATTRIBUTE = "data-paseo-markdown-ignore";
+export const MARKDOWN_COPY_UNWRAP_ATTRIBUTE = "data-paseo-markdown-unwrap";
+export const MARKDOWN_COPY_LIST_START_ATTRIBUTE = "data-paseo-markdown-list-start";
+export const MARKDOWN_COPY_LANGUAGE_ATTRIBUTE = "data-paseo-markdown-language";
+export const MARKDOWN_COPY_ALIGN_ATTRIBUTE = "data-paseo-markdown-align";
+
+export const markdownCopyDataSet = {
+  blockquote: { paseoMarkdownTag: "blockquote" },
+  br: { paseoMarkdownTag: "br" },
+  code: { paseoMarkdownTag: "code" },
+  h1: { paseoMarkdownTag: "h1" },
+  h2: { paseoMarkdownTag: "h2" },
+  h3: { paseoMarkdownTag: "h3" },
+  h4: { paseoMarkdownTag: "h4" },
+  h5: { paseoMarkdownTag: "h5" },
+  h6: { paseoMarkdownTag: "h6" },
+  hr: { paseoMarkdownTag: "hr" },
+  ignore: { paseoMarkdownIgnore: "true" },
+  li: { paseoMarkdownTag: "li" },
+  ol: { paseoMarkdownTag: "ol" },
+  p: { paseoMarkdownTag: "p" },
+  pre: { paseoMarkdownTag: "pre" },
+  s: { paseoMarkdownTag: "s" },
+  strong: { paseoMarkdownTag: "strong" },
+  em: { paseoMarkdownTag: "em" },
+  table: { paseoMarkdownTag: "table" },
+  tbody: { paseoMarkdownTag: "tbody" },
+  td: { paseoMarkdownTag: "td" },
+  th: { paseoMarkdownTag: "th" },
+  thead: { paseoMarkdownTag: "thead" },
+  tr: { paseoMarkdownTag: "tr" },
+  ul: { paseoMarkdownTag: "ul" },
+  unwrap: { paseoMarkdownUnwrap: "true" },
+} as const;
+
+export type MarkdownCopyInlineTag = "br" | "code" | "em" | "s" | "strong";
+
+export function markdownCopyOrderedListDataSet(start: unknown) {
+  return {
+    ...markdownCopyDataSet.ol,
+    paseoMarkdownListStart: String(start ?? 1),
+  } as const;
+}
+
+export function markdownCopyCodeBlockDataSet(language: string | null | undefined) {
+  const fenceLanguage = language?.trim().split(/\s+/)[0];
+  return {
+    ...markdownCopyDataSet.pre,
+    ...(fenceLanguage ? { paseoMarkdownLanguage: fenceLanguage } : {}),
+  } as const;
+}
+
+export function markdownCopyTableCellDataSet(tag: "td" | "th", style: unknown) {
+  const alignment =
+    typeof style === "string"
+      ? style.match(/(?:^|;)\s*text-align\s*:\s*(left|right|center)/i)?.[1]
+      : null;
+  return {
+    ...markdownCopyDataSet[tag],
+    ...(alignment ? { paseoMarkdownAlign: alignment.toLowerCase() } : {}),
+  } as const;
+}
diff --git a/packages/app/src/assistant-selection-copy/surface.tsx b/packages/app/src/assistant-selection-copy/surface.tsx
new file mode 100644
index 000000000..4f6464c19
--- /dev/null
+++ b/packages/app/src/assistant-selection-copy/surface.tsx
@@ -0,0 +1,14 @@
+import type { ReactNode } from "react";
+import { View, type StyleProp, type ViewStyle } from "react-native";
+
+interface AssistantSelectionCopySurfaceProps {
+  children: ReactNode;
+  style?: StyleProp<ViewStyle>;
+}
+
+export function AssistantSelectionCopySurface({
+  children,
+  style,
+}: AssistantSelectionCopySurfaceProps) {
+  return <View style={style}>{children}</View>;
+}
diff --git a/packages/app/src/assistant-selection-copy/surface.web.tsx b/packages/app/src/assistant-selection-copy/surface.web.tsx
new file mode 100644
index 000000000..280688b61
--- /dev/null
+++ b/packages/app/src/assistant-selection-copy/surface.web.tsx
@@ -0,0 +1,32 @@
+import { useCallback, type ClipboardEvent, type CSSProperties, type ReactNode } from "react";
+import { View, type StyleProp, type ViewStyle } from "react-native";
+import { createAssistantSelectionClipboardContent } from "./content.web";
+
+interface AssistantSelectionCopySurfaceProps {
+  children: ReactNode;
+  style?: StyleProp<ViewStyle>;
+}
+
+const DISPLAY_CONTENTS: CSSProperties = { display: "contents" };
+
+export function AssistantSelectionCopySurface({
+  children,
+  style,
+}: AssistantSelectionCopySurfaceProps) {
+  const handleCopy = useCallback((event: ClipboardEvent<HTMLDivElement>) => {
+    const content = createAssistantSelectionClipboardContent(window.getSelection());
+    if (!content) {
+      return;
+    }
+
+    event.preventDefault();
+    event.clipboardData.setData("text/plain", content.plainText);
+    event.clipboardData.setData("text/html", content.html);
+  }, []);
+
+  return (
+    <div onCopy={handleCopy} style={DISPLAY_CONTENTS}>
+      <View style={style}>{children}</View>
+    </div>
+  );
+}
diff --git a/packages/app/src/components/highlighted-code-block.tsx b/packages/app/src/components/highlighted-code-block.tsx
index dd3200b3b..6506bf0ae 100644
--- a/packages/app/src/components/highlighted-code-block.tsx
+++ b/packages/app/src/components/highlighted-code-block.tsx
@@ -11,6 +11,10 @@ import { useIsCompactFormFactor } from "@/constants/layout";
 import { syntaxTokenStyleFor } from "@/styles/syntax-token-styles";
 import { CODE_SURFACE_DATASET } from "@/styles/code-surface";
 import { highlightToKeyedLines, type KeyedLine } from "@/utils/highlight-cache";
+import {
+  markdownCopyCodeBlockDataSet,
+  markdownCopyDataSet,
+} from "@/assistant-selection-copy/markup";
 
 interface HighlightedCodeBlockProps {
   code: string;
@@ -63,6 +67,10 @@ export const HighlightedCodeBlock = React.memo(function HighlightedCodeBlock({
     [inheritedStyles, textStyle],
   );
   const renderedCode = useMemo(() => stripTerminalFenceNewline(code), [code]);
+  const copyDataSet = useMemo(
+    () => ({ ...CODE_SURFACE_DATASET, ...markdownCopyCodeBlockDataSet(language) }),
+    [language],
+  );
 
   const keyedLines = useMemo<KeyedLine[] | null>(
     () => highlightToKeyedLines(renderedCode, fenceLanguageToExtension(language)),
@@ -79,14 +87,18 @@ export const HighlightedCodeBlock = React.memo(function HighlightedCodeBlock({
   return (
     <View
       style={containerStyle}
-      dataSet={CODE_SURFACE_DATASET}
+      dataSet={copyDataSet}
       onPointerEnter={handlePointerEnter}
       onPointerLeave={handlePointerLeave}
     >
       {keyedLines ? (
-        <MarkdownTextSpan style={innerTextStyle}>{renderCodeSegments(keyedLines)}</MarkdownTextSpan>
+        <MarkdownTextSpan style={innerTextStyle} copyTag="code">
+          {renderCodeSegments(keyedLines)}
+        </MarkdownTextSpan>
       ) : (
-        <MarkdownTextSpan style={innerTextStyle}>{renderedCode}</MarkdownTextSpan>
+        <MarkdownTextSpan style={innerTextStyle} copyTag="code">
+          {renderedCode}
+        </MarkdownTextSpan>
       )}
       <CopyButton getCode={getCode} visible={controlsVisible} />
     </View>
@@ -195,6 +207,7 @@ const CopyButton = React.memo(function CopyButton({ getCode, visible }: CopyButt
       accessibilityRole="button"
       accessibilityLabel={copied ? t("message.actions.copied") : t("message.actions.copyCode")}
       hitSlop={8}
+      dataSet={markdownCopyDataSet.ignore}
     >
       {({ hovered }) => {
         const iconColor = hovered
diff --git a/packages/app/src/components/markdown-text.android.tsx b/packages/app/src/components/markdown-text.android.tsx
index d2cb0864e..f444d916b 100644
--- a/packages/app/src/components/markdown-text.android.tsx
+++ b/packages/app/src/components/markdown-text.android.tsx
@@ -7,10 +7,12 @@ import {
   type TextStyle,
   type ViewStyle,
 } from "react-native";
+import type { MarkdownCopyInlineTag } from "@/assistant-selection-copy/markup";
 
 interface MarkdownTextSpanProps {
   style?: StyleProp<TextStyle>;
   monoSurface?: boolean;
+  copyTag?: MarkdownCopyInlineTag;
   children: ReactNode;
   onPress?: TextProps["onPress"];
   accessibilityRole?: TextProps["accessibilityRole"];
diff --git a/packages/app/src/components/markdown-text.ios.tsx b/packages/app/src/components/markdown-text.ios.tsx
index b3b6607e0..1b2eb405c 100644
--- a/packages/app/src/components/markdown-text.ios.tsx
+++ b/packages/app/src/components/markdown-text.ios.tsx
@@ -13,10 +13,12 @@ import {
   iosMarkdownTextIsSelectable,
   useMarkdownTextSurface,
 } from "@/components/markdown-text-selection";
+import type { MarkdownCopyInlineTag } from "@/assistant-selection-copy/markup";
 
 interface MarkdownTextSpanProps {
   style?: StyleProp<TextStyle>;
   monoSurface?: boolean;
+  copyTag?: MarkdownCopyInlineTag;
   children: ReactNode;
   // Links route through this span too (see assistant-file-links/link.tsx). A
   // plain <Text> nested in the paragraph UITextView is dropped, so the link
diff --git a/packages/app/src/components/markdown-text.web.tsx b/packages/app/src/components/markdown-text.web.tsx
index 8d5f9fa95..0cb89f0cf 100644
--- a/packages/app/src/components/markdown-text.web.tsx
+++ b/packages/app/src/components/markdown-text.web.tsx
@@ -8,10 +8,12 @@ import {
   type ViewStyle,
 } from "react-native";
 import { CODE_SURFACE_DATASET } from "@/styles/code-surface";
+import { markdownCopyDataSet, type MarkdownCopyInlineTag } from "@/assistant-selection-copy/markup";
 
 interface MarkdownTextSpanProps {
   style?: StyleProp<TextStyle>;
   monoSurface?: boolean;
+  copyTag?: MarkdownCopyInlineTag;
   children: ReactNode;
   // Web links use the <a>/Pressable path in link.tsx, not this span, so these
   // are accepted for prop-shape parity with the native variants and forwarded
@@ -28,17 +30,23 @@ interface MarkdownTextSpanProps {
 export function MarkdownTextSpan({
   style,
   monoSurface,
+  copyTag,
   children,
   onPress,
   accessibilityRole,
 }: MarkdownTextSpanProps) {
+  const dataSet = useMemo(() => {
+    if (copyTag && (monoSurface || copyTag === "code")) {
+      return { ...CODE_SURFACE_DATASET, ...markdownCopyDataSet[copyTag] };
+    }
+    if (copyTag) {
+      return markdownCopyDataSet[copyTag];
+    }
+    return monoSurface ? CODE_SURFACE_DATASET : undefined;
+  }, [copyTag, monoSurface]);
+
   return (
-    <Text
-      dataSet={monoSurface ? CODE_SURFACE_DATASET : undefined}
-      style={style}
-      onPress={onPress}
-      accessibilityRole={accessibilityRole}
-    >
+    <Text dataSet={dataSet} style={style} onPress={onPress} accessibilityRole={accessibilityRole}>
       {children}
     </Text>
   );
@@ -57,5 +65,9 @@ const MARKDOWN_PARAGRAPH_RESET: ViewStyle = {};
 // elements via CSS user-select, so no UITextView equivalent is needed.
 export function MarkdownParagraphView({ paragraphStyle, children }: MarkdownParagraphViewProps) {
   const style = useMemo(() => [paragraphStyle, MARKDOWN_PARAGRAPH_RESET], [paragraphStyle]);
-  return <View style={style}>{children}</View>;
+  return (
+    <View style={style} dataSet={markdownCopyDataSet.p}>
+      {children}
+    </View>
+  );
 }
diff --git a/packages/app/src/components/message.tsx b/packages/app/src/components/message.tsx
index b67d6acf7..2cc7cb402 100644
--- a/packages/app/src/components/message.tsx
+++ b/packages/app/src/components/message.tsx
@@ -28,7 +28,8 @@ import {
   cloneElement,
 } from "react";
 import type { ComponentType, ReactNode } from "react";
-import { MarkdownIt, type ASTNode, type RenderRules } from "react-native-markdown-display";
+import type MarkdownIt from "markdown-it";
+import { type ASTNode, type RenderRules } from "react-native-markdown-display";
 import MaskedView from "@react-native-masked-view/masked-view";
 import {
   Circle,
@@ -71,6 +72,7 @@ import { markdownNodeContainsType } from "@/utils/markdown-ast";
 import { useStableEvent } from "@/hooks/use-stable-event";
 import { HighlightedCodeBlock } from "@/components/highlighted-code-block";
 import { splitMarkdownBlocks } from "@/utils/split-markdown-blocks";
+import { createAssistantMarkdownParser } from "@/utils/assistant-markdown-parser";
 import { formatDuration, formatMessageTimestamp } from "@/utils/time";
 import { writeMarkdownToRichClipboard } from "@/utils/rich-clipboard";
 import { getDefaultMarkdownClipboardEnvironment } from "@/utils/rich-clipboard-default-environment";
@@ -103,6 +105,12 @@ import { RewindMenu, type RewindMode } from "@/components/rewind/rewind-menu";
 import { useRewindAgentMutation } from "@/components/rewind/use-rewind-agent-mutation";
 import { AssistantForkMenu, type AssistantForkTarget } from "@/components/assistant-fork-menu";
 import { useRetainedPanelActive } from "@/components/retained-panel";
+import {
+  markdownCopyDataSet,
+  markdownCopyOrderedListDataSet,
+  markdownCopyTableCellDataSet,
+  type MarkdownCopyInlineTag,
+} from "@/assistant-selection-copy/markup";
 export type { InlinePathTarget } from "@/assistant-file-links";
 export type { AssistantForkTarget };
 
@@ -880,10 +888,7 @@ function AssistantMarkdownImage({
   );
 }
 
-function getInlineCodeAutoLinkUrl(
-  markdownParser: ReturnType<typeof MarkdownIt>,
-  content: string,
-): string | null {
+function getInlineCodeAutoLinkUrl(markdownParser: MarkdownIt, content: string): string | null {
   const trimmed = content.trim();
   if (!trimmed) {
     return null;
@@ -928,6 +933,7 @@ function getMarkdownLinkSource(node: AssistantMarkdownAstNode): AssistantFileLin
   return {
     href: typeof node.attributes?.href === "string" ? node.attributes.href : "",
     text: getMarkdownNodeText(node),
+    title: typeof node.attributes?.title === "string" ? node.attributes.title : undefined,
     markup: node.markup,
     sourceInfo: node.sourceInfo,
     sourceType: node.sourceType === "inline-code" ? "inline-code" : undefined,
@@ -1364,6 +1370,7 @@ interface MarkdownInheritedTextProps {
   textStyle: TextStyle;
   style?: StyleProp<TextStyle>;
   monoSurface?: boolean;
+  copyTag?: MarkdownCopyInlineTag;
   children: ReactNode;
 }
 
@@ -1372,6 +1379,7 @@ function MarkdownInheritedText({
   textStyle,
   style: overrideStyle,
   monoSurface,
+  copyTag,
   children,
 }: MarkdownInheritedTextProps) {
   const style = useMemo(
@@ -1387,6 +1395,7 @@ function MarkdownInheritedText({
   return (
     <MarkdownTextSpan
       monoSurface={monoSurface}
+      copyTag={copyTag}
       style={style}
       onPress={linkPress?.onPress}
       accessibilityRole={linkPress?.accessibilityRole}
@@ -1410,13 +1419,27 @@ function MarkdownListItemContent({ contentStyle, children }: MarkdownListItemCon
 
 interface MarkdownListViewProps {
   baseStyle: ViewStyle;
+  copyTag: "ol" | "ul";
+  orderedStart?: unknown;
   spacing: { marginTop: number; marginBottom: number };
   children: ReactNode;
 }
 
-function MarkdownListView({ baseStyle, spacing, children }: MarkdownListViewProps) {
+function MarkdownListView({
+  baseStyle,
+  copyTag,
+  orderedStart,
+  spacing,
+  children,
+}: MarkdownListViewProps) {
   const style = useMemo(() => [baseStyle, spacing], [baseStyle, spacing]);
-  return <View style={style}>{children}</View>;
+  const copyDataSet =
+    copyTag === "ol" ? markdownCopyOrderedListDataSet(orderedStart) : markdownCopyDataSet.ul;
+  return (
+    <View style={style} dataSet={copyDataSet}>
+      {children}
+    </View>
+  );
 }
 
 export const AssistantMessage = memo(function AssistantMessage({
@@ -1428,18 +1451,7 @@ export const AssistantMessage = memo(function AssistantMessage({
   client,
   spacing = "default",
 }: AssistantMessageProps) {
-  const markdownParser = useMemo(() => {
-    const parser = MarkdownIt({ typographer: true, linkify: true });
-    const defaultValidateLink = parser.validateLink.bind(parser);
-    parser.validateLink = (url: string) => {
-      if (url.trim().toLowerCase().startsWith("file://")) {
-        return true;
-      }
-
-      return defaultValidateLink(url);
-    };
-    return parser;
-  }, []);
+  const markdownParser = useMemo(createAssistantMarkdownParser, []);
 
   const fileLinkActions = useAssistantFileLinkActions();
   const handleMarkdownLinkPress = useStableEvent((url: string) => {
@@ -1451,6 +1463,103 @@ export const AssistantMessage = memo(function AssistantMessage({
 
   const markdownRules = useMemo<RenderRules>(() => {
     return {
+      heading1: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading1} dataSet={markdownCopyDataSet.h1}>
+          {children}
+        </View>
+      ),
+      heading2: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading2} dataSet={markdownCopyDataSet.h2}>
+          {children}
+        </View>
+      ),
+      heading3: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading3} dataSet={markdownCopyDataSet.h3}>
+          {children}
+        </View>
+      ),
+      heading4: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading4} dataSet={markdownCopyDataSet.h4}>
+          {children}
+        </View>
+      ),
+      heading5: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading5} dataSet={markdownCopyDataSet.h5}>
+          {children}
+        </View>
+      ),
+      heading6: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View key={node.key} style={styles._VIEW_SAFE_heading6} dataSet={markdownCopyDataSet.h6}>
+          {children}
+        </View>
+      ),
+      blockquote: (
+        node: ASTNode,
+        children: ReactNode[],
+        _parent: ASTNode[],
+        styles: MarkdownStyles,
+      ) => (
+        <View
+          key={node.key}
+          style={styles._VIEW_SAFE_blockquote}
+          dataSet={markdownCopyDataSet.blockquote}
+        >
+          {children}
+        </View>
+      ),
+      hr: (node: ASTNode, _children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
+        <View key={node.key} style={styles._VIEW_SAFE_hr} dataSet={markdownCopyDataSet.hr} />
+      ),
+      table: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
+        <View key={node.key} style={styles._VIEW_SAFE_table} dataSet={markdownCopyDataSet.table}>
+          {children}
+        </View>
+      ),
+      thead: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
+        <View key={node.key} style={styles._VIEW_SAFE_thead} dataSet={markdownCopyDataSet.thead}>
+          {children}
+        </View>
+      ),
+      tbody: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
+        <View key={node.key} style={styles._VIEW_SAFE_tbody} dataSet={markdownCopyDataSet.tbody}>
+          {children}
+        </View>
+      ),
+      tr: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
+        <View key={node.key} style={styles._VIEW_SAFE_tr} dataSet={markdownCopyDataSet.tr}>
+          {children}
+        </View>
+      ),
       text: (
         node: ASTNode,
         _children: ReactNode[],
@@ -1497,6 +1606,7 @@ export const AssistantMessage = memo(function AssistantMessage({
       ) => (
         <MarkdownInheritedText
           key={node.key}
+          copyTag="strong"
           inheritedStyles={inheritedStyles}
           textStyle={styles.strong}
         >
@@ -1512,6 +1622,7 @@ export const AssistantMessage = memo(function AssistantMessage({
       ) => (
         <MarkdownInheritedText
           key={node.key}
+          copyTag="em"
           inheritedStyles={inheritedStyles}
           textStyle={styles.em}
         >
@@ -1527,6 +1638,7 @@ export const AssistantMessage = memo(function AssistantMessage({
       ) => (
         <MarkdownInheritedText
           key={node.key}
+          copyTag="s"
           inheritedStyles={inheritedStyles}
           textStyle={styles.s}
         >
@@ -1547,7 +1659,7 @@ export const AssistantMessage = memo(function AssistantMessage({
         _parent: ASTNode[],
         styles: MarkdownStyles,
       ) => (
-        <MarkdownTextSpan key={node.key} style={styles.hardbreak}>
+        <MarkdownTextSpan key={node.key} style={styles.hardbreak} copyTag="br">
           {"\n"}
         </MarkdownTextSpan>
       ),
@@ -1642,6 +1754,7 @@ export const AssistantMessage = memo(function AssistantMessage({
         return (
           <MarkdownInheritedText
             key={node.key}
+            copyTag="code"
             inheritedStyles={inheritedStyles}
             textStyle={styles.code_inline}
             monoSurface
@@ -1659,6 +1772,7 @@ export const AssistantMessage = memo(function AssistantMessage({
         <MarkdownListView
           key={node.key}
           baseStyle={styles.bullet_list}
+          copyTag="ul"
           spacing={getMarkdownListSpacing(node, parent)}
         >
           {children}
@@ -1673,6 +1787,8 @@ export const AssistantMessage = memo(function AssistantMessage({
         <MarkdownListView
           key={node.key}
           baseStyle={styles.ordered_list}
+          copyTag="ol"
+          orderedStart={node.attributes?.start}
           spacing={getMarkdownListSpacing(node, parent)}
         >
           {children}
@@ -1689,8 +1805,10 @@ export const AssistantMessage = memo(function AssistantMessage({
         const contentStyle = isOrdered ? styles.ordered_list_content : styles.bullet_list_content;
 
         return (
-          <View key={node.key} style={styles.list_item}>
-            <Text style={iconStyle}>{marker}</Text>
+          <View key={node.key} style={styles.list_item} dataSet={markdownCopyDataSet.li}>
+            <Text style={iconStyle} dataSet={markdownCopyDataSet.ignore}>
+              {marker}
+            </Text>
             <MarkdownListItemContent contentStyle={contentStyle}>
               {children}
             </MarkdownListItemContent>
@@ -1699,12 +1817,22 @@ export const AssistantMessage = memo(function AssistantMessage({
       },
       th: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
         <MarkdownTableCellText key={node.key}>
-          <View style={styles._VIEW_SAFE_th}>{children}</View>
+          <View
+            style={styles._VIEW_SAFE_th}
+            dataSet={markdownCopyTableCellDataSet("th", node.attributes?.style)}
+          >
+            {children}
+          </View>
         </MarkdownTableCellText>
       ),
       td: (node: ASTNode, children: ReactNode[], _parent: ASTNode[], styles: MarkdownStyles) => (
         <MarkdownTableCellText key={node.key}>
-          <View style={styles._VIEW_SAFE_td}>{children}</View>
+          <View
+            style={styles._VIEW_SAFE_td}
+            dataSet={markdownCopyTableCellDataSet("td", node.attributes?.style)}
+          >
+            {children}
+          </View>
         </MarkdownTableCellText>
       ),
       paragraph: (
diff --git a/packages/app/src/types/turndown-plugin-gfm.d.ts b/packages/app/src/types/turndown-plugin-gfm.d.ts
new file mode 100644
index 000000000..a6c0855cf
--- /dev/null
+++ b/packages/app/src/types/turndown-plugin-gfm.d.ts
@@ -0,0 +1,5 @@
+declare module "turndown-plugin-gfm" {
+  import type TurndownService from "turndown";
+
+  export const gfm: TurndownService.Plugin;
+}
diff --git a/packages/app/src/utils/__tests__/split-markdown-blocks.test.ts b/packages/app/src/utils/__tests__/split-markdown-blocks.test.ts
index 2a12f80e4..3de5188e3 100644
--- a/packages/app/src/utils/__tests__/split-markdown-blocks.test.ts
+++ b/packages/app/src/utils/__tests__/split-markdown-blocks.test.ts
@@ -67,6 +67,14 @@ describe("splitMarkdownBlocks", () => {
     ]);
   });
 
+  it("keeps a loose nested list in its outer list block", () => {
+    expect(
+      splitMarkdownBlocks(
+        "Before\n\n3. Outer three\n\n   7. Inner seven\n   8. Inner eight\n\nAfter",
+      ),
+    ).toEqual(["Before", "3. Outer three\n\n   7. Inner seven\n   8. Inner eight", "After"]);
+  });
+
   it("treats triple newlines as a split point and filters empty blocks", () => {
     expect(splitMarkdownBlocks("First paragraph\n\n\nSecond paragraph")).toEqual([
       "First paragraph",
diff --git a/packages/app/src/utils/assistant-markdown-parser.ts b/packages/app/src/utils/assistant-markdown-parser.ts
new file mode 100644
index 000000000..4a8493ca8
--- /dev/null
+++ b/packages/app/src/utils/assistant-markdown-parser.ts
@@ -0,0 +1,15 @@
+import MarkdownIt from "markdown-it";
+
+export function createAssistantMarkdownParser(): MarkdownIt {
+  const parser = new MarkdownIt({
+    html: false,
+    linkify: true,
+    typographer: true,
+  });
+  const defaultValidateLink = parser.validateLink.bind(parser);
+
+  parser.validateLink = (url: string) =>
+    url.trim().toLowerCase().startsWith("file://") || defaultValidateLink(url);
+
+  return parser;
+}
diff --git a/packages/app/src/utils/rich-clipboard.test.ts b/packages/app/src/utils/rich-clipboard.test.ts
index 129d87c23..cae8e5d44 100644
--- a/packages/app/src/utils/rich-clipboard.test.ts
+++ b/packages/app/src/utils/rich-clipboard.test.ts
@@ -74,6 +74,20 @@ describe("createMarkdownClipboardContent", () => {
     expect(content.html).not.toContain('href="javascript:');
     expect(content.html).toContain("&lt;script&gt;");
   });
+
+  it("preserves assistant file links without allowing unsafe link schemes", () => {
+    const content = createMarkdownClipboardContent(
+      [
+        "[file](file:///tmp/paseo%20notes.md#L4)",
+        '[javascript](javascript:alert("x"))',
+        "[data](data:text/html,unsafe)",
+        "[vbscript](vbscript:msgbox(1))",
+      ].join("\n\n"),
+    );
+
+    expect(content.html).toContain('<a href="file:///tmp/paseo%20notes.md#L4">file</a>');
+    expect(content.html).not.toMatch(/href="(?:javascript|data|vbscript):/);
+  });
 });
 
 describe("writeMarkdownToRichClipboard", () => {
diff --git a/packages/app/src/utils/rich-clipboard.ts b/packages/app/src/utils/rich-clipboard.ts
index ad4030333..427e443f4 100644
--- a/packages/app/src/utils/rich-clipboard.ts
+++ b/packages/app/src/utils/rich-clipboard.ts
@@ -1,10 +1,6 @@
-import MarkdownIt from "markdown-it";
+import { createAssistantMarkdownParser } from "./assistant-markdown-parser";
 
-const markdownRenderer = new MarkdownIt({
-  html: false,
-  linkify: true,
-  typographer: true,
-});
+const markdownRenderer = createAssistantMarkdownParser();
 
 type ClipboardMimeType = "text/plain" | "text/html";
 
diff --git a/packages/app/src/utils/split-markdown-blocks.ts b/packages/app/src/utils/split-markdown-blocks.ts
index 3d7e831ad..636642e12 100644
--- a/packages/app/src/utils/split-markdown-blocks.ts
+++ b/packages/app/src/utils/split-markdown-blocks.ts
@@ -1,7 +1,6 @@
-function getFenceDelimiter(line: string) {
-  const match = /^( {0,3})(`{3,}|~{3,})/.exec(line);
-  return match?.[2] ?? null;
-}
+import MarkdownIt from "markdown-it";
+
+const markdownBlockParser = new MarkdownIt();
 
 export function splitMarkdownBlocks(text: string): string[] {
   if (text.length === 0) {
@@ -10,43 +9,32 @@ export function splitMarkdownBlocks(text: string): string[] {
 
   const blocks: string[] = [];
   let currentLines: string[] = [];
-  let activeFenceCharacter: "`" | "~" | null = null;
-  let activeFenceLength = 0;
   let sawBlockSeparator = false;
+  const lines = text.split("\n");
+  const structuralBlankLines = getStructuralBlankLines(text, lines);
 
-  for (const line of text.split("\n")) {
+  for (const [index, line] of lines.entries()) {
     const isBlankLine = line.trim().length === 0;
 
-    if (!activeFenceCharacter && isBlankLine) {
+    if (isBlankLine && structuralBlankLines.has(index)) {
+      currentLines.push(line);
+      continue;
+    }
+
+    if (isBlankLine) {
       if (currentLines.length > 0) {
         sawBlockSeparator = true;
       }
       continue;
     }
 
-    if (!activeFenceCharacter && sawBlockSeparator) {
+    if (sawBlockSeparator) {
       blocks.push(currentLines.join("\n"));
       currentLines = [];
       sawBlockSeparator = false;
     }
 
     currentLines.push(line);
-
-    const fenceDelimiter = getFenceDelimiter(line);
-    if (!fenceDelimiter) {
-      continue;
-    }
-
-    if (!activeFenceCharacter) {
-      activeFenceCharacter = fenceDelimiter[0] as "`" | "~";
-      activeFenceLength = fenceDelimiter.length;
-      continue;
-    }
-
-    if (fenceDelimiter[0] === activeFenceCharacter && fenceDelimiter.length >= activeFenceLength) {
-      activeFenceCharacter = null;
-      activeFenceLength = 0;
-    }
   }
 
   if (currentLines.length > 0) {
@@ -55,3 +43,19 @@ export function splitMarkdownBlocks(text: string): string[] {
 
   return blocks.filter((block) => block.length > 0);
 }
+
+function getStructuralBlankLines(text: string, lines: string[]): Set<number> {
+  const blankLines = new Set<number>();
+  for (const token of markdownBlockParser.parse(text, {})) {
+    if (token.level !== 0 || !token.map) {
+      continue;
+    }
+    const [start, end] = token.map;
+    for (let index = start; index < end - 1; index += 1) {
+      if (lines[index]?.trim().length === 0) {
+        blankLines.add(index);
+      }
+    }
+  }
+  return blankLines;
+}
diff --git a/packages/server/src/server/agent/providers/mock-load-test-agent.ts b/packages/server/src/server/agent/providers/mock-load-test-agent.ts
index 2b39fcc53..12d90b5db 100644
--- a/packages/server/src/server/agent/providers/mock-load-test-agent.ts
+++ b/packages/server/src/server/agent/providers/mock-load-test-agent.ts
@@ -614,6 +614,7 @@ export class MockLoadTestAgentSession implements AgentSession {
   private pendingPermissions = new Map<string, AgentPermissionRequest>();
   private modeId: string | null;
   private modelId: string | null;
+  private readonly assistantResponse: string | null;
   private readonly rewindError: string | null;
   private remainingPromptRejections: number;
 
@@ -622,6 +623,10 @@ export class MockLoadTestAgentSession implements AgentSession {
     this.logger = options.logger;
     this.modeId = options.config.modeId ?? MOCK_LOAD_TEST_MODE_ID;
     this.modelId = options.config.model ?? MOCK_LOAD_TEST_DEFAULT_MODEL_ID;
+    this.assistantResponse =
+      typeof options.config.featureValues?.mockAssistantResponse === "string"
+        ? options.config.featureValues.mockAssistantResponse
+        : null;
     this.rewindError =
       typeof options.config.featureValues?.mockRewindError === "string"
         ? options.config.featureValues.mockRewindError
@@ -687,6 +692,8 @@ export class MockLoadTestAgentSession implements AgentSession {
     const scheduleTurn = () => {
       if (shouldEmitTurnFailure(prompt)) {
         this.scheduleFailedTurn(turn);
+      } else if (this.assistantResponse !== null) {
+        this.scheduleSettledAssistantTurn(turn, this.assistantResponse);
       } else if (structuredBranchName) {
         this.scheduleSettledAssistantTurn(turn, JSON.stringify(structuredBranchName));
       } else if (settledAssistantImageMarkdown) {